Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2001(6): 0863-0866
DOI: 10.1055/s-2001-13406
DOI: 10.1055/s-2001-13406
PAPER
© Georg Thieme Verlag Stuttgart · New York
Enantioselective Preparation of a Novel Chiral 1,2-Diamine
Further Information
Received
6 February 2001
Publication Date:
15 October 2004 (online)
Publication History
Publication Date:
15 October 2004 (online)
Abstract
A short enantioselective preparation of (1S,2S)-trans-1,2-diamino-3-cyclohexene using a double [3,3]-sigmatropic rearrangement of an allylic bis(imidate) is described (Overman rearrangement). The starting chiral diol is conveniently obtained by enzymatic resolution.
Key words
1,2-diamines - enzymes - rearrangements - chiral resolution
- For excellent reviews, see:
-
1a
Bennani YL.Hanessian S. Chem. Rev. 1997, 97: 3161 -
1b
Fache F.Schultz E.Tommasino ML.Lemaire M. Chem. Rev. 2000, 100: 2159 -
1c
Lucet D.DeGall T.Mioskowski C. Angew. Chem., Int. Ed. Engl. 1998, 37: 2580 - For some recent applications of chiral diamines see:
-
2a
Alexakis A.Tomassini A.Chouillet C.Roland S.Mangeney P.Bernardinelli G. Angew. Chem., Int. Ed. 2000, 112: 4259 -
2b
Li X.Schenkel LB.Kozlowski MC. Org. Lett. 2000, 2: 875 -
3a
Reetz M.Schmitz A. Tetrahedron Lett. 1999, 40: 2741 -
3b
Alvaro G.Grilli S.Martelli G.Savoia D. Eur. J. Org. Chem. 1999, 1523 -
3c
Alexakis A.Aujard I.Mangeney P. Synlett 1998, 873 -
3d
Alexakis A.Aujard I.Mangeney P. Synlett 1998, 875 -
3e
Enders D.Schiffers R. Synthesis 1996, 53 -
3f
Enders D.Meiers M. Angew. Chem., Int. Ed. Engl. 1996, 35: 2261 -
3g
Enders D.Wiedemann J. Synthesis 1996, 1443 -
3h
Larrow JF.Jacobsen EN.Gao Y.Hong Y.Xie X.Zepp CM. J. Org. Chem. 1994, 59: 1939 - 4
Demay S.Harms K.Knochel P. Tetrahedron Lett. 1999, 40: 4981 -
5a
Overman LE. J. Am. Chem. Soc. 1976, 98: 2901 -
5b
Overman LE. Acc. Chem. Res. 1980, 13: 218 -
5c
Overman LE.Zipp GG. J. Org. Chem. 1997, 62: 2288 - 6
Kowalski CJ.Weber AE.Fields KW. J. Org. Chem. 1982, 77: 5088 - 7
Corey EJ.Bakshi RK.Shibata S.Chen C.Singh VK. J. Am. Chem. Soc. 1987, 109: 7925 - 8
Whu KM.Okamura WH. J. Org. Chem. 1990, 55: 4025 - 9
Sabol JS.Cregge RJ. Tetrahedron Lett. 1989, 30: 3377 -
10a
Posternak T.Friedli H. Helv. Chem. Acta 1953, 36: 251 -
10b
Uemura S.Miyoshi H.Tabata A.Okano M. Tetrahedron 1981, 37: 291 -
11a
Laumen K.Breitgloff D.Seemayer R.Schneider MP. J. Chem. Soc., Chem. Commun. 1989, 148 -
11b
Fang C.Ogawa T.Suemune H.Sakai K. Tetrahedron: Asymmetry 1991, 2: 389